Hannah decides to quit teaching and leave her boyfriend, Jack, to return home to Chicago and pursue a career as a writer. On the flight home to Chicago, Hannah meets and helps Marty deal with his fear of flying, and he tells her about a research job opening at Chicago Monthly, the magazine where he works as a writer. Hannah goes to the magazine to apply for the job, meets the editor, and is challenged to write a 2,000-word article on "the tortilla wars: does Chicago prefer corn or flour?" by 9 o'clock the following morning.

Hannah's old boyfriend and Marty's ex-college roommate are one in the same person, and Jack tries to convince her that he has changed. Meanwhile, Hannah and Marty are working on a story that will expose a charity scam.